Trifluoroacetic acid → HCID 10211420, compound

HRID 1835584Notes

Reaction equation

HRID 1835584 reaction equation
C([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=2)=[C:12]([CH:40]=1)[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:25]([CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[C:24]3[CH:32]=[CH:33][C:34]([C:36]([O:38][CH3:39])=[O:37])=[CH:35][C:23]=3[N:22]=2)=[CH:17][CH:16]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[ClH:47].[C:6]([C:8]1[CH:9]=[CH:10][C:11]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=2)=[C:12]([CH:40]=1)[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[N:25]([CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[C:24]3[CH:32]=[CH:33][C:34]([C:36]([O:38][CH3:39])=[O:37])=[CH:35][C:23]=3[N:22]=2)=[CH:19][CH:20]=1)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10122322HCID 10122322, compound

Product 1

HCID 10211420HCID 10211420, compoundYield 194.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-{4-[5-tert-butoxycarbonyl-2-(4-chlorophenyl)-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate (3.5 g) obtained in Example 245 was dissolved in dichloromethane (35 ml), and trifluoroacetic acid (35 ml) was added. The mixture was stirred for 1 hr at room temperature and the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and 4N hydrochloric acid-ethyl acetate was added. The precipitated crystals were collected by filtration and dried under reduced pressure to give the title compound (3.3 g, yield 97%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. addition4N hydrochloric acid-ethyl acetate was added
  4. filtrationThe precipitated crystals were collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-b19be5c205844e7b8e3c89008e174201
Source dataset
uspto-grants-2004_08
Patent number
US06770666B2

Reaction notes

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